It was a dinner party in Miami back in 2015. Caroline Wozniacki, the tennis star known for her defensive grit, was out past her usual 8 p.m. bedtime. David Lee, then an NBA powerhouse with the Golden State Warriors, was there too. Most people think these high-profile romances are orchestrated by PR teams or high-end dating apps. Honestly? They were just introduced by mutual friends and hit it off because they both understood the weird, high-pressure world of professional sports.
Fast forward to 2026, and the David Lee and Caroline Wozniacki partnership has become something of a blueprint for life after the final whistle. They aren't just "retired athletes." They are a case study in how to navigate massive fame, a "zone defense" household of three kids, and a real estate portfolio that would make a hedge fund manager blush.
The Meet-Cute and That 2019 Tuscany Wedding
When they first met, Lee actually forgot to get her number. He had to follow her out of the restaurant to the Fisher Island Ferry just to secure a way to talk to her again. That's a bold move. It worked. By the time they got engaged in Bora Bora in 2017—with an 8.8-carat diamond that probably has its own zip code—the world knew this wasn't just a fleeting "sports couple" moment.
They got married in 2019 at Castiglion del Bosco in Tuscany. It was the kind of wedding that defines "A-list." Serena Williams was a bridesmaid. Pau Gasol and Jesse Palmer were there. But the standout moment wasn't the guest list; it was Lee’s speech. He joked about the "miracle" of Caroline being awake past 7:30 p.m. for their first date. It’s that kind of grounded, self-aware humor that has kept them in the public’s good graces while other celebrity marriages crumbled under the spotlight.
Switching to "Zone Defense": Life with Three Kids
For years, it was just the two of them traveling the globe for tournaments and games. Then came Olivia in June 2021. Then James in October 2022. By early 2025, the couple announced they were "officially switching to zone defense."
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Max Wozniacki Lee arrived on July 26, 2025.
Living in 2026 with three children under the age of five is a chaotic reality, even if you have millions in the bank. Caroline has been open about the shift. In a recent podcast appearance on the Nothing Major Show, she admitted that while her tennis DNA makes it hard to say "never" to another comeback, having three small kids is a "full-time job."
The Wozniacki-Lee Roster:
- Olivia Wozniacki Lee: Born June 11, 2021. The first-born who often appeared on court during Caroline's 2023-2024 comeback.
- James Wozniacki Lee: Born October 24, 2022.
- Max Wozniacki Lee: Born July 26, 2025. The latest addition who effectively sealed the "zone defense" era.
The $42 Million Real Estate Flex
You can’t talk about David Lee and Caroline Wozniacki without mentioning Fisher Island. It’s the wealthiest zip code in the United States, accessible only by ferry or boat. It's the kind of place where privacy is the ultimate currency.
In early 2024, the couple listed their 7,000-square-foot penthouse for a staggering $42.5 million. They had bought it for $18.7 million just three years prior. That is a masterclass in real estate timing. The place is a temple of "quiet luxury"—oak herringbone floors, a 5,000-square-foot terrace, and views of the Miami skyline that look like a green-screen effect.
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Whether they sold it for the full asking price or kept it as part of their growing portfolio, it signaled their transition from athletes to serious business players. David Lee, who earned over $90 million during his NBA career, and Caroline, who took home $35 million in prize money alone, aren't just sitting on their cash. They are active investors.
Is the Tennis Comeback Actually Over?
This is the question that haunts every Caroline Wozniacki fan in 2026. After her initial retirement in 2020, she made a "shock" return in 2023. She proved she still had it, reaching the round of 16 at the US Open and showing the world that "mom strength" is a real thing.
But as of right now, the racket seems to be staying in the bag.
Caroline has hinted that her future is in broadcasting. She’s already done stints with ESPN and the Tennis Channel, and she's good at it. She’s insightful, blunt, and knows the modern game better than almost anyone in the booth. She recently mentioned that working "selected weeks" a year while spending the rest of the time with David and the kids is the "perfect balance."
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David is the one who usually pushes for her to keep playing. He’s her biggest hype man, often pointing out that her "protected ranking" could get her into any major tournament she wants. But for now, the family's focus has shifted from Grand Slams to school runs.
Why This Duo Works Where Others Fail
Most sports couples fail because of the "two suns" problem—two massive egos competing for the same light. David and Caroline avoided this by staggering their retirements. David was already transitioning out of the NBA when Caroline was still at the top of her game. When she retired the first time, he was there to support the transition to motherhood. When she wanted to go back in 2023, he became the primary "stay-at-home" support.
It also helps that they are both financially literate. They didn't blow their earnings on a "lifestyle" that required them to stay in the spotlight. Instead, they built a wall of privacy on Fisher Island and focused on long-term wealth.
Actionable Insights for Following the Couple in 2026:
- Watch the Booth: Look for Caroline as a regular fixture during the Grand Slam broadcasts (Australian Open, Wimbledon, US Open). Her analysis is frequently more technical and "player-centric" than traditional commentators.
- Real Estate Tracking: Keep an eye on South Florida high-end listings. The couple has a knack for flipping ultra-luxury properties in the Miami area.
- The "Nothing Major" Podcast: If you want the most candid updates on their family life, this show (hosted by John Isner and Sam Querrey) is where Caroline tends to drop the most "real" information about her future.
- Health and Wellness: Caroline has been a vocal advocate for living with rheumatoid arthritis. Expect her to continue her work with pharmaceutical partnerships and health awareness, showing how she manages a high-impact life with a chronic condition.
The story of David Lee and Caroline Wozniacki isn't about the trophies anymore. It's about the "second act." In a world where athletes often struggle to find their identity after the stadium lights go out, these two seem to have found theirs in a quiet, incredibly expensive corner of Florida, raising three kids and occasionally reminding the world why they were champions in the first place.